Aza-Henry Reactions on C-Alkyl Substituted Aldimines

The reactivity of C-CH(3) substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse ele...

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Autores principales: Pelagalli, Alessia, Pellacani, Lucio, Scandozza, Elia, Fioravanti, Stefania
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273577/
https://www.ncbi.nlm.nih.gov/pubmed/27271579
http://dx.doi.org/10.3390/molecules21060723
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author Pelagalli, Alessia
Pellacani, Lucio
Scandozza, Elia
Fioravanti, Stefania
author_facet Pelagalli, Alessia
Pellacani, Lucio
Scandozza, Elia
Fioravanti, Stefania
author_sort Pelagalli, Alessia
collection PubMed
description The reactivity of C-CH(3) substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF(3) aldimines, they gave the aza-Henry addition only when ZrCl(4) was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity.
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spelling pubmed-62735772018-12-28 Aza-Henry Reactions on C-Alkyl Substituted Aldimines Pelagalli, Alessia Pellacani, Lucio Scandozza, Elia Fioravanti, Stefania Molecules Article The reactivity of C-CH(3) substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF(3) aldimines, they gave the aza-Henry addition only when ZrCl(4) was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity. MDPI 2016-06-02 /pmc/articles/PMC6273577/ /pubmed/27271579 http://dx.doi.org/10.3390/molecules21060723 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Pelagalli, Alessia
Pellacani, Lucio
Scandozza, Elia
Fioravanti, Stefania
Aza-Henry Reactions on C-Alkyl Substituted Aldimines
title Aza-Henry Reactions on C-Alkyl Substituted Aldimines
title_full Aza-Henry Reactions on C-Alkyl Substituted Aldimines
title_fullStr Aza-Henry Reactions on C-Alkyl Substituted Aldimines
title_full_unstemmed Aza-Henry Reactions on C-Alkyl Substituted Aldimines
title_short Aza-Henry Reactions on C-Alkyl Substituted Aldimines
title_sort aza-henry reactions on c-alkyl substituted aldimines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273577/
https://www.ncbi.nlm.nih.gov/pubmed/27271579
http://dx.doi.org/10.3390/molecules21060723
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